Diethyl Ether → 1-[2-(Phenylmethoxy)-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzene

HRID 235719Notes

Reaction equation

HRID 235719 reaction equation
[CH2:1]([C:15]1[CH:45]=[CH:44][C:18]([O:19][CH2:20][CH:21]([OH:43])[CH2:22][O:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CCO[CH2:49][CH3:50]>CN(C)C=O>[C:49]1([CH2:50][O:43][CH:21]([CH2:22][O:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:20][O:19][C:18]2[CH:17]=[CH:16][C:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:45][CH:44]=2)[CH:16]=[CH:15][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 202184241-(4-Tetradecylphenoxy)-3-(triphenylmethoxy)-2-propanol

Product 1

HCID 202183791-[2-(Phenylmethoxy)-3-(triphenylmethoxy)propoxy]-4-tetradecylbenzeneYield 198.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of about 13.78 g of 1-(4-tetradecyl phenoxy)-3-(triphenylmethoxy)-2-propanol in about 45 ml of dimethylformamide was added a suspension of about 1.426 g of ether pre-washed sodium hydride in about 10 ml of dimethylformamide, followed by a solution of about 4.06 g of benzylbromide in about 5 ml of dimethylformamide. The mixture was stirred under argon for about 3 hours, quenched very slowly with water and extracted twice with about 50% ether in hexane. The organic layer was dried, filtered and the solvents removed, giving about 15.7 g of the desired title compound.

Workup

  1. washpre-washed sodium hydride in about 10 ml of dimethylformamide
  2. customquenched very slowly with water
  3. extractionextracted twice with about 50% ether in hexane
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customthe solvents removed

Sources & evidence

ORD record
ord-4cc3b1b8df354baca4b1fdf41a892d0f
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Reaction notes

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